2-(3-羟基-2-氧代-1H-吲哚-3-基)乙酸 | 57061-17-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2-(3-羟基-2-氧代-1H-吲哚-3-基)乙酸
• 英文名称: 2,3-dihydro-3-hydroxy-2-oxo-1H-indole-3-acetic acid
• 英文别名: 2-(3-hydroxy-2-oxoindolin-3-yl)acetic acid；2,3-dioxoindole-3-acetic acid；2-(3-dioxindolyl)acetic acid；dioxindole-3-acetic acid；(3-hydroxy-2-oxo-2,3-dihydro-indol-3-yl)-acetic acid；(+/-)-Dioxindol-3-essigsaeure-(6)；1H-Indole-3-acetic acid, 2,3-dihydro-3-hydroxy-2-oxo-；2-(3-hydroxy-2-oxo-1H-indol-3-yl)acetic acid
• CAS: 57061-17-3；63389-31-1
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: MHLHEINWUCSPTL-UHFFFAOYSA-N

物化性质

• 沸点：
  550.4±50.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-(3-羟基-2-氧代-1H-吲哚-3-基)乙酸 、 三甲基硅烷化重氮甲烷 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 2-(3-羟基-2-氧代-1H-吲哚-3-基)乙酸甲酯
  参考文献：
  名称：

  丙二酸直接催化不对称合成β-羟基酸

  摘要：

  开发了镍（II）催化由丙二酸和酮不对称合成β-羟基酸的方法，这首次揭示了丙二酸在手性羧酸的合成中的合成作用。重要的是，该方法的合成潜力通过快速构建头孢菌素A，紫杉醇B，十字花青素和大米代谢产物得到了进一步证明。

  DOI：

  10.1021/acs.orglett.5b02891
• 作为产物：
  描述：

  3-吲哚丙酸 在 18-冠醚-6 作用下， 以 二甲基亚砜 为溶剂， 反应 8.3h， 生成 3-(2-Formamidobenzoyl)propionsaeure 、 2-(3-羟基-2-氧代-1H-吲哚-3-基)乙酸
  参考文献：
  名称：

  Itakura, Koichi; Uchida, Koji; Kawakishi, Shunro, Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 3, p. 488 - 493

  摘要：

  DOI：

文献信息

• A Diamino Alcohol Catalyzed Enantioselective Crossed Aldol Reaction of Acetaldehyde with Isatins - A Concise Total Synthesis of Antitumor Agents
  作者：Ummareddy Venkata Subba Reddy、Madhu Chennapuram、Kento Seki、Chigusa Seki、Bheemreddy Anusha、Eunsang Kwon、Yuko Okuyama、Koji Uwai、Michio Tokiwa、Mitsuhiro Takeshita、Hiroto Nakano

  DOI：10.1002/ejoc.201700399

  日期：2017.7.17

  metal-free total syntheses of antitumor and antiviral agents with the tryptanthrin architecture, that is, phaitanthrin B and cephalanthrin A, along with the biologically active indolidine alkaloids chimonamidine and donaxaridine as well as the formal synthesis of CPC-1. The highly enantioselective outcome of this catalytic crossed aldol reaction was evaluated by calculating the Gibbs free energies of the possible

  已使用一系列简单的二氨基醇催化剂开发了靛红衍生物和乙醛的对映选择性交叉羟醛缩合反应，以高化学收率（高达95％）和光学纯度（高达92％）提供了3-取代的3-羟基吲哚-2-酮。  ee）。本方案的合成潜力已通过具有锥虫素结构的抗肿瘤药和抗病毒药的简明，对映体选择性，无保护基团和无过渡金属的总合成得到了证明，这就是类泛素B和脑啡肽A以及具有生物活性的吲哚啶生物碱，mon胺和多那西啶以及CPC-1的正式合成。通过计算可能的过渡态的吉布斯自由能，评估了该催化的交叉羟醛反应的高度对映选择性。
• PESTICIDAL COMPOSITION COMPRISING INDOLE DERIVATES
  申请人：Bednarek Pawel

  公开号：US20090028796A1

  公开（公告）日：2009-01-29

  The present invention is directed to pesticidal compositions comprising indole derivatives. These indole derivatives are especially active against phytopathogenic fungi. Furthermore, the invention relates to the use of indole derivatives for the production of pesticides and the use of the compositions according to the invention as pesticides. The present invention is also directed to a process for producing a pesticidal composition and to pesticidal compositions prepared by this process. In addition, the invention relates to a process for preventing or combating pests and to a process for protecting plants against pests, especially against phytopathogenic fungi. Further, the invention is directed to plants or seeds as well as objects or materials which have been protected against pests by treatment with a composition according to the invention. Further, the invention is directed to a method for identifying a substance having pesticidal activity. Further, the invention is directed to a method of identifying the mode of action of and/or of providing binding proteins for a pesticidal compound of the present invention. Finally, the invention is directed to a method for diagnosing pest infection of a plant and to the use of a pesticidal compound of the present invention as diagnostic markers.

  本发明涉及包含吲哚衍生物的杀虫组合物。这些吲哚衍生物特别对植物病原真菌具有活性。此外，本发明涉及使用吲哚衍生物制备杀虫剂以及使用本发明中的组合物作为杀虫剂。本发明还涉及制备杀虫组合物的过程以及通过该过程制备的杀虫组合物。此外，本发明还涉及预防或对抗害虫的过程以及保护植物免受害虫，特别是植物病原真菌的过程。此外，本发明还涉及经过本发明中的组合物处理后受到保护的植物或种子以及物体或材料。本发明还涉及识别具有杀虫活性的物质的方法。此外，本发明还涉及识别本发明中杀虫化合物的作用方式和/或提供结合蛋白的方法。最后，本发明涉及诊断植物害虫感染的方法以及使用本发明中的杀虫化合物作为诊断标记的方法。
• Use of compounds that are able to increase the serum IGF-1 level for the preparation of a therapeutical composition for treatment of various disease states associated with a reduced IGF-1 serum level in humans and animals
  申请人：VEIJLEN N.V.

  公开号：US10716778B2

  公开（公告）日：2020-07-21

  The present disclosure relates to the use of one or more compounds that are capable of increasing the serum level of insulin-like growth factor 1 (IGF-1) for the preparation of a therapeutical composition, in particular, in the form of a food supplement, for the treatment of subjects suffering from serious fatigue and exhausting symptoms, burn-out and chronic fatigue syndrome. The same composition can also be used by patients suffering from depression, Alzheimer disease, irritated bowel syndrome, osteoporosis, type 2 diabetes, or for anti-aging, immune therapy and recovery after exercise. The composition also has a use in veterinary applications for increasing the growth and immunity in animals.

  本公开涉及一种或多种能够提高血清中胰岛素样生长因子1（IGF-1）水平的化合物用于制备治疗组合物，特别是以食品补充剂的形式，用于治疗患有严重疲劳和疲惫症状、倦怠和慢性疲劳综合征的患者。同样的组合物还可用于抑郁症、老年痴呆症、肠易激综合征、骨质疏松症、2 型糖尿病患者，或用于抗衰老、免疫疗法和运动后恢复。该成分还可用于兽医领域，提高动物的生长速度和免疫力。
• Acetylphosphonate as a Surrogate of Acetate or Acetamide in Organocatalyzed Enantioselective Aldol Reactions
  作者：Jie Guang、Qunsheng Guo、John Cong-Gui Zhao

  DOI：10.1021/ol301270w

  日期：2012.6.15

  Highly enantioselective aldol reactions of acetylphosphonates and activated carbonyl compounds was realized with cinchona alkaloid derived catalysts, in which the acetylphosphonate was directly used as an enolate precursor for the first time. The aldol product obtained was converted in situ to its corresponding ester or amide through methanolysis or aminolysis. The overall process may be viewed as formal highly enantioselective acetate or acetamide aldol reactions, which are very difficult to achieve directly with organocatalytic methods.
• In vitro Oxidation of Indoleacetic Acid by Crude Enzyme from Rice Husk—An Aspect of Preharvest Sprouting
  作者：Tadahiro Kato、Norihiro Tomita、Masahiro Hoshikawa、Kazuhiro Ehara、Jyunko Shima、Norindo Takahashi、Hiroshi Sugiyama

  DOI：10.3987/com-97-s(n)12

  日期：——